Synthesis of N-tert.-butoxycarbonyl(α-phenyl)aminomethylphenoxyacetic acid for use as a handle in solid-phase synthesis of peptide α-carboxamides

doi:10.1111/J.1399-3011.1981.TB03006.X

Paper

Synthesis of N-tert.-butoxycarbonyl(α-phenyl)aminomethylphenoxyacetic acid for use as a handle in solid-phase synthesis of peptide α-carboxamides

Published Jan 12, 2009 · S. Gaehde, G. Matsueda

International Journal of Peptide and Protein Research

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Abstract

N-tert.-butoxycarbonyl-aminomethyl( alpha-phenyl)phenoxyacetic acid was synthesized and found to be suitable for use as a handle in the solid-phase synthesis of peptide alpha-carboxamides. This handle was prepared with an 82% yield when N-tert.-butoxycarbonyl-( rho-hydroxy)benzhydrylamine was treated with excess sodium iodoacetate under alkaline conditions. In stability studies the linkage between the C-terminal amino acid and the handle was found to be resistant to acidolysis in 50% TFA/CH2Cl2 (less than 1% loss after 10h). Upon treatment for 30 min with HF:anisole(9:1) at 0 degrees, 92% cleavage of glycinamide from Gly-handle-resin was obtained. In a test synthesis of a peptide alpha-carboxamide, pyroglutamylhistidylprolinamide was synthesized in 83% yield. Two other handles, tert.-butoxycarbonyl-aminomethylphenoxyacetic acid and N-tert.-butoxycarbonyl-aminomethylphenyloxymethylphenoxyacetic acid, were also synthesized but found to be unsuitable for carboxamide synthesis under the same conditions of solid-phase synthesis.

Study Snapshot

N-tert.-butoxycarbonyl-aminomethyl(alpha-phenyl)phenoxyacetic acid is a suitable handle for solid-phase synthesis of peptide alpha-carboxamides, with high yield and stability.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Synthesis of N-tert.-butoxycarbonyl(α-phenyl)aminomethylphenoxyacetic acid for use as a handle in solid-phase synthesis of peptide α-carboxamides

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